1,2-Dimethoxyethane → HCID 89629895, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-acetyl-4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbohydrazide (0.40 g, 0.85 mmol) in ethylene glycol dimethyl ether (10 mL), was added P2S5 (378 mg, 1.70 mmol). The resulting solution was stirred for 1 hour at 50° C., then concentrated in vacuo and extracted with ethyl acetate (×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was purified by chromatography using silica gel, eluting with 1-100% ethyl acetate/petroleum ether. The product was collected and concentrated in vacuo to afford 2-methyl-5-(4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-1,3,4-thiadiazole as a yellow oil. LRMS (ESI) calc'd for C21H25N6O3SSi [M+H]+: 469, found 469.

Provenance & Evidence